#65 | The Conversation Most Leaders Avoid—And Why It’s Costing You Respect

Leadership isn’t hard because of strategy.

It’s hard because of people. And one poorly handled conversation can damage trust, shut down a team member, or create tension that lasts for months.

In this episode of Lead With SWAGGER, Jennifer Sukalo shares the two powerful leadership traits that make difficult conversations easier, more productive, and far more impactful.

Inside this episode:

• The moment in meetings that tells you a conversation must happen
• Why most leaders escalate issues instead of addressing them directly
• The two questions that will transform how you prepare for difficult conversations
• A real story where humility changed an entire client relationship

If you’ve ever avoided a conversation you knew you needed to have… this episode is for you.

Because sometimes the most powerful leadership moment…
starts with a single conversation.

Transcript

SPEAKER_00 0:10

Have you ever been in a meeting where someone said something that completely shut another person down? And you could feel it instantly. The room went quiet, the energy shifted, and the person on the receiving end just withdrew. In that moment, you knew something needed to be addressed. But then the question becomes: do you say something? Do you ignore it? Do you escalate it? Or do you step into the uncomfortable space and have the conversation most leaders try to avoid? Welcome back to Lead with Swagger, the podcast where we don't shy away from the difficult conversations, we lean into them, we learn from them and we grow through them. I'm your host, Jennifer Socallo, and I'm really glad you're here today because the conversation we're about to have might just shift the way you think about leadership and the way you show up in some of the hardest moments as a leader. Now let's be honest with each other for a moment. Leadership is hard. And it's not because of strategy, it's not because of budgets. Leadership is hard because it deals with people, and people are complex. They bring their experiences, fears, ambitions, insecurities, and cultural norms into every interaction. Which means there will inevitably be moments where things go sideways. Someone says something they shouldn't, someone feels disrespected, someone shuts down. And in those moments, leadership isn't about having the perfect answer. It's about having the courage to have the right conversation. Today we're going to talk about two keys to having difficult conversations and a simple strategy you can use to prepare for them. So you can walk into those moments with confidence and clarity instead of hesitation. Because here's the truth: great leaders aren't defined by the easy conversations, they're defined by the ones most people try to avoid. And here's something that took me years of working with leaders across the globe to truly, really comprehend and understand. Our role is to create opportunities for people to see things differently, to plant seeds, seeds of awareness, seeds of reflection, seeds of growth. Because change only happens when someone chooses it for themselves. I learned this in spades after facilitating leadership programs around the world. I could deliver the most powerful workshop, the most engaging experiences, have the most transformative conversations, and none of that mattered. Because at the end of the day, those moments were simply planting seeds. People first had to recognize that change might be needed. Then they had to decide that change was worth it, and only then would they take action. Now let's walk through a situation together. Imagine you're in a meeting, an employee said something that completely embarrasses another colleague. It's dismissive, it's demeaning. And the moment it happens, the person on the receiving end just shuts down. You can see it. They stop contributing, they withdraw from the conversation, the energy in the room shifts. Now, if you've ever experienced this, you know exactly what I'm talking about. So what do you do? Option A, you decide after the meeting that you're gonna go to HR and report the behavior. Option B, you choose to speak directly with the individual who made the comment following the meeting and ask what they were hoping to accomplish, as well as sharing the impact that comment had, your observations. Option C, you decide to go to their boss after the meeting and ask how they would like to handle the situation. Now, over the years, when I've asked leaders this kind of question, people chose all three options. Some driven by fear, some by company protocol, some by past experiences. But there is a clear best option. Do you know which one it is? Option B. Have the conversation directly. Why? Because if we put ourselves in the other person's shoes, most of us would want someone to pull us aside and let us know the impact our behavior had. That gives us a chance to learn, to adjust, to grow before it escalates, before it becomes a bigger issue. So why do we avoid these conversations? Most people avoid these conversations because of what? Any thoughts? If you were thinking fear, you would be spot on. It is typically fear-based, fear of conflict, fear of being wrong, fear of how it's going to be perceived, fear of making things worse. But there's another reason that sometimes is even more powerful. Ego. Sometimes we walk into conversations thinking they were wrong, I'm right. They need to understand what they did and the impact of what they did. And the moment we enter a conversation with that mindset, we've already lost. And when people feel that way, they don't listen, they defend. Now there are two keys to having difficult conversations. Here's what actually works. In my experience, two things can change everything: curiosity and humility. Now let's start with curiosity. Curiosity means acknowledging that we don't always have the full story. You saw something through your lens, your experience, your values, your cultural background, but you don't know what was happening for them. Maybe they felt threatened, maybe they felt unheard, maybe they were trying to establish authority, or maybe they didn't even realize what they did. Curiosity allows you to ask questions instead of making accusations. Now let's talk about humility. Humility means recognizing that you are not the judge and jury. You are not there to deliver a verdict, you are there to create awareness and open dialogue. And when you approach a conversation with humility, something powerful happens. People lower their defenses, they feel safe enough to reflect. Now, before walking into a difficult conversation, I ask myself two simple questions. Question one: What do I hope to accomplish with this interaction? To what end? What am I trying to achieve or accomplish? Not what I want to say, not how I want to prove a point, but what outcome do I genuinely desire? Is it understanding? Is it awareness? Is it strengthening the team? What is it that I aim to achieve? That question forces me to become intentional about my interaction. Question two. What information do I know that might influence how I approach this conversation? For example, maybe the person I'm speaking with tends to operate from a competitive mindset. They may feel like everyone in the room is competing for recognition, credit, or promotions. In that case, I need to approach the conversation carefully. Because if they feel accused, they'll immediately go into defense mode. But if I approach them with curiosity and collaboration, we can have a productive conversation. And to be honest, things had gotten rocky. They hadn't gone well through the development and piloting stages of the program, and tensions were quite high. And during one of the meetings, I said something very simple. I said, I am really sorry you've had to go through this. My team and I are committed to making this right and ensuring a successful outcome. What can we do to help you feel more confident about our approach moving forward? Now, do you know what she said? She said, I was the very first person who had apologized. Now, this completely blew my mind. But that moment, that moment changed everything. The relationship shifted instantly. She knew I cared and she knew I was taking ownership. And shortly after that conversation, she asked me to take over leadership of the entire account. Not because I had all the answers, but because I approached the conversation and the entire situation with humility and curiosity. Now, here's the truth: fear, pride, and ego get in our way more times than we care to admit. They convince us that we need to be right. We need to defend ourselves. We need to prove something. But leadership isn't about proving your right, it's about creating environments where people can grow. And sometimes that growth starts with a simple conversation. So here's my challenge for you this week. Think about one conversation you've been avoiding. You know the one. It probably already popped into your head. The feedback you haven't given, the issue you haven't addressed, the tension you've been hoping will just resolve itself. Now take 10 minutes and prepare using the two questions we talked about already. Ask yourself, what do I hope to accomplish with this conversation? And what information do I know that might help me approach this with empathy and understanding? Then walk into the conversation with curiosity and humility, not judgment, not ego, just a genuine desire to understand and help someone see things differently. Because that's what great leaders do. They don't force change, they create conditions where change becomes possible. Now, if this episode resonated with you, I'd love for you to do two things. First, hit the follow button on Lead with Swagger so you never miss an opportunity to learn and grow. And second, share this episode with another leader who might be struggling with a difficult conversation right now. You never know who might need to hear this. And if you are looking to elevate your leadership, strengthen your presence, and show up with greater confidence and impact, I'd love to connect with you. You can reach out to me directly on LinkedIn or book a discovery conversation with me to explore how we might work together. Because leadership doesn't have to feel lonely. And sometimes the right conversation can change everything. Until next time, remember this: leave your ego at the door. You are not the judge and jury, you are the leader who creates space for people to grow. And that is what it means to lead with swagger.